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Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon.

ABSTRACT: We report here the total synthesis of 11-epi-lyngbouilloside aglycon. Our strategy features a Boeckman-type esterification followed by a RCM to form the 14-membered ring macrolactone and a late-stage side chain introduction via a Wittig olefination. Overall, the final product was obtained in 20 steps and 2% overall yield starting from commercially available 3-methyl-but-3-enol. Most importantly, the strategy employed is versatile enough to eventually allow us to complete the synthesis of the natural product and irrevocably confirm its structure.

SUBMITTER: Kolleth A

PROVIDER: S-EPMC4977289 | biostudies-other | 2016

REPOSITORIES: biostudies-other

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Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon.

Kolleth Amandine A Gebauer Julian J ElMarrouni Abdelatif A Lebeuf Raphael R Prévost Céline C Brohan Eric E Arseniyadis Stellios S Cossy Janine J

Frontiers in chemistry 20160809

We report here the total synthesis of 11-epi-lyngbouilloside aglycon. Our strategy features a Boeckman-type esterification followed by a RCM to form the 14-membered ring macrolactone and a late-stage side chain introduction via a Wittig olefination. Overall, the final product was obtained in 20 steps and 2% overall yield starting from commercially available 3-methyl-but-3-enol. Most importantly, the strategy employed is versatile enough to eventually allow us to complete the synthesis of the nat ...[more]

PMID: 27556024

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